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I Crossdressing For Fun

Personal Stories, Advice, and Support 749 People

    Pleasure Perfect

    I have been a cross dresser from a very young age. In puberty and ever since it has been a huge sexual turn on for me. I used to dress up as often as possible and still do. It always gets me excited to the point, when I was younger I had to relieve myself. Now that I'm older I...
    zymack zymack 56-60, M 5 Responses Mar 9, 2012

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    Crossdresser From Time To Time.

    There's times that I don't wear any women's clothes with the exception of pantyhose or ocassionally some women's shorts. But there are times that everyday I just have the big urge to slip into a blouse and a skirt and some women's shoes and a wig. It just feels so great to dress...
    montserrat70 montserrat70 41-45, M 1 Response Mar 10, 2013

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    Me Too

    I wear all dresses of women. ... But I don't want to be feminine. I wear them only just for fun and pleasure.
    lingarielover lingarielover 31-35, M 2 Responses Apr 12, 2012

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    Relaxing

    I find crossdressing fun. It is the only time of the day where I can relax. It is simple and easy for me. I have a favorite outfit to wear, panties, bra, and silk nightie. Just having that material on is worth putting in the time.
    sharonlynne sharonlynne 41-45, M 3 Responses Jan 22, 2013

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    My Wife's Nighties

    I enjoy wearing my wife's nighties when she is not around, as it gets me in the right mood for when she comes home. The feeling of the material rubbing against my bare flesh is a real turn on. I have a couple of favourite nighties that i always go for, but tonight i went for...
    toril34 toril34 51-55, M 2 Responses Jul 20, 2012

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    Crossdressing..it's Not Just A Hobby Anymore

    From our first meeting my wife knew I found being smooth and hairless (save for a pink puff above my erect clitty)and attired in satin and nylon and silky feeling attire to be a turn on I was driven to. From my early teens on, the fetish to visually assume (and eventually...
    CYNDIMC CYNDIMC 31-35 3 Responses Sep 23, 2012

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    I Love Crossdressing

    I crossdress because it is fun, it feels good, it is highly erotic and I have the best ******* I have ever had. I love looking at photos of beautiful Ladyboys while I am dressed in very sensual sexy outfits, pantyhose and high heels and make love to myself while imagining making...
    candiceldubonet candiceldubonet 46-50, T Apr 21, 2012

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    First Time In Front Of Friends

    Like some boys and men, I have tried cross-dressing on occasion. As a teenager, I would get sexually aroused by it. I would wear (let's say a girl's swimsuit), look at myself in the mirror and try to imagine a girl in that certain outfit and that would excite me. These occasions...
    LittleMelissa LittleMelissa 61-65, M 27 Responses Apr 6, 2012

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    Started Late

    I was raised in a family environment that was pretty straight and church going. If I had desires out of the norm, they were thoroughly suppressed. As an adult, I worked in a very macho world, any display of feminine characteristics would have caused serious repercussions for me...
    Pat398 Pat398 56-60 1 Response Jul 14, 2012

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    Waiting To Dress Up

    I live in a boarding home now I like to dress up in private and can`t do it here I have not had a bra or panties on in about a year 1/2. I dream of it really. last night in a dream my wife was measuring me for a bra.
    crosserJonie crosserJonie 51-55, M May 23, 2012

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    Deeper Than The Fun

    living fulltime as a female now, taking natural hormones to change my body, and planning on having srs, but i still love dressing like a woman every single day. the fun part for me is showing off my inner female in public. people for the most part take me for a genetic female...
    Mizsuzy Mizsuzy 46-50, T 2 Responses May 2, 2012

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    First Time In Front Of Friends...(adding To It)

    I was in a dream state sitting at my friends' dinning room table. It was my alone time, as my friends were preparing dinner in the kitchen. I was a princess waiting to be served by my two friends. My dress was a powder blue and a style very similar to what Princess Diana (bless...
    LittleMelissa LittleMelissa 61-65, M 3 Responses Apr 9, 2012

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    For The Fun

    I started fully cross-dressing when I was about 23yrs old after wearing just tights/pantyhose from about13/14, I think it is rather nice to cross-dress for the fun of it as there is a wider range of items you can wear when you are cross-dressing as a woman.
    xdpaul xdpaul 56-60, M Jun 22, 2012

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    Love To Crossdress

    I think of crossdressing all the time. Wearing panties, lingerie, pantyhose, stockings, skirts, and other womans clothing is always on my mind. Crossdressing just makes me feel so alive, happy, calm, relaxed and always puts me in a good mood, as well as making me more excited...
    pantiescouple pantiescouple 26-30 2 Responses Feb 17, 2012

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    Happiness...

    It is a happy time, those moments or those days where I am free to dress in my "good" clothes. There is a relaxation to shedding the jeans and tee in trade for the blouse and skirt one that hasn't been experienced in any other situation. Now then, I am a straight, married male...
    DonnaSt DonnaSt 66-70, M 6 Responses Jul 14, 2012

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    People should be less intense about this. :) i am good everything is good. things that I don't know, i will leave it as it is.
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    Keniaga838 Keniaga838 31-35, M 1 Response Sep 2

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    I want guys to accept me for me; for my quirky personality and my annoying laugh. I don't like heels and dresses. I'm a jeans, t shirt and slipper girl. I want guys to accept that...
    caramelcuteness caramelcuteness 26-30, F 11 Responses Sep 5

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    This is a famous joke. Not true, but fun to repeat. Sam walked into the locker room to change into his softball uniform. The guys spotted the bra he was wearing and shouted "What...
    Robertredlips Robertredlips 56-60, M Aug 22

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    I love crossdressing the feel of a sexy bra and thong are the best and sexy mini skirt
    harley80cu harley80cu 41-45, M 2 Responses Sep 11

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    I was caught cross-dressing. I sometimes travel to different cities for work. In nice cities (San Francisco) I rent a motorcycle on my days off and ride to the nice places. In SF...
    Robertredlips Robertredlips 56-60, M 1 Response Aug 27

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    When I was 14 I started crossdressing. My Mother and older Sister were gone quite a bit. One day after school I went home and started putting on my sisters clothes. Bra, panties...
    Stephaniegirl226 Stephaniegirl226 36-40, M 6 Responses Sep 13

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    anyone looking for friends to chat about crossdressing, etc. please feel free to add me.
    girlyAndrea1987 girlyAndrea1987 26-30, M 1 Response 5 days ago

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    One of those fascinating but as yet unanswerable nature versus nurture conundrums. What is interesting is that for some the crossdressing impulse expresses itself very early...
    Barrbara Barrbara 56-60 3 Responses 6 days ago

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    My *** in my new panties... Looking for a daddy :)
    samanthacd21 samanthacd21 18-21, T 2 Responses Aug 26

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    I was caught by my mum a few months ago. I was wearing some of her lingerie black tights and black heels strutting around the house. I didnt hear her come in and i turned around...
    tomcd95 tomcd95 18-21 7 Responses Aug 29

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    I started collage again yesterday and wore me pretty green panties and a lot of people saw and this guy was cute told me to follow him so i did and we dressed up toghter and i tide...
    LOVERPANTIES LOVERPANTIES 18-21, M 6 Responses Aug 29

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    I was alone that day got bored at home I was watching from window on road one girl was walking I saw her in salwar she was so feminine there was no one on road suddenly she makes...
    sronal sronal 22-25, F Sep 9

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    i keep passing over this experience as i feel embarrassed or maybe ashamed that this is even a part of me. i was good at hiding this side of me from the time i was seven years old...
    trailsonrails trailsonrails 51-55, M 2 Responses 3 days ago

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    The last time..? Maybe? So it's been a while since my last post (December) and I was thinking about coming out. Well, things took a hold of itself in it's own way and so much has...
    elliecarr elliecarr 18-21, T 8 Responses Aug 22

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    My friend came over to my house and he went to my room I forgot to put my pink thong away and he asked if I wear it I told him yes and he asked if I fully dressed I once again said...
    Pantyhoseboy1 Pantyhoseboy1 18-21, M 5 Responses Aug 23

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    I have always wanted to get caught cross-dressing and be horribly humiliated. This story you are now reading is not true, but I am sharing it as if it was true: Last Friday night...
    Robertredlips Robertredlips 56-60, M 1 Response Aug 27

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    Hello, crossdressing slave here. Looking for Mistress or Master. Must be between 15-22 :) xx
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